trifluoromethanesulfonyl 2,3,4,6-tetra-O-methyl-α-D-mannopyranoside | 197631-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trifluoromethanesulfonyl 2,3,4,6-tetra-O-methyl-α-D-mannopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl] trifluoromethanesulfonate
• CAS: 197631-82-6
• 化学式: C₁₁H₁₉F₃O₈S
• 分子量: 368.328
• InChiKey: RPZNYYCDDYUPJR-FHNUBNKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonyl 2,3,4,6-tetra-O-methyl-α-D-mannopyranoside 以 二氯甲烷-D2 为溶剂， 反应 0.83h， 生成 1-deoxy-2,3,4,6-tetra-O-methyl-D-mannopyranosyl 2-chloropyridinium triflate
  参考文献：
  名称：

  使用活化的二苯基锍试剂进行脱水糖基化。C(1)-半缩醛活化的范围、模式和反应性糖基中间体的检测

  摘要：

  描述了使用三氟甲磺酸酐和二苯亚砜的试剂组合与 1-羟基糖基供体直接脱水糖基化的方法的开发。一锅偶联法是一种适用于多种碳水化合物偶联伙伴的简便方法。氧 18 标记研究与碳水化合物活化的第一步一致，即形成异头氧锍中间体。当 2,3,4,6-四-O-甲基-d-吡喃甘露糖作为糖基供体被激活时，这种活性糖基物质 (35) 在低温 NMR 实验中是可观察到的。当脱水糖基化反应在三氟甲磺酸清除剂 2-氯吡啶存在下进行时，

  DOI：

  10.1021/ja993595a
• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-methyl-1-deoxy-1-thio-α-D-mannopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二氯甲烷-D2 为溶剂， 反应 0.5h， 生成 trifluoromethanesulfonyl 2,3,4,6-tetra-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and ¹H, ¹³C, and ¹⁹F NMR Spectroscopic Investigation

  摘要：

  The title question is addressed by low-temperature H-1, C-13, and F-19 NMR spectroscopies in CD2Cl2 as well as by the preparation of authentic samples from glycopyranosyl bromides and AgOTf. At -78 degrees C glycosyl triflates are cleanly generated with either nonparticipating or particpating protecting groups at O-2. The glycosyl triflates identified in this manner were allowed to react with methanol, resulting in the formation of methyl glycosides. Glycosyl triflates were generated at -78 degrees C in CD2Cl2 and allowed to warm gradually until decomposition was detected by H-1 and F-19 NMR spectroscopy. The decomposition temperature and products are functions of the protecting groups employed.

  DOI：

  10.1021/ja971239r

文献信息

• Dehydrative Glycosylation with Activated Diphenyl Sulfonium Reagents. Scope, Mode of <i>C</i>(1)-Hemiacetal Activation, and Detection of Reactive Glycosyl Intermediates
  作者：Brian A. Garcia、David Y. Gin

  DOI：10.1021/ja993595a

  日期：2000.5.1

  The development of a method for direct dehydrative glycosylations with 1-hydroxyglycosyl donors employing the reagent combination of triflic anhydride and diphenyl sulfoxide is described. The one-pot coupling method is a facile process which is applicable to a variety of carbohydrate coupling partners. Oxygen-18-labeling studies are consistent with the first step in carbohydrate activation being the

  描述了使用三氟甲磺酸酐和二苯亚砜的试剂组合与 1-羟基糖基供体直接脱水糖基化的方法的开发。一锅偶联法是一种适用于多种碳水化合物偶联伙伴的简便方法。氧 18 标记研究与碳水化合物活化的第一步一致，即形成异头氧锍中间体。当 2,3,4,6-四-O-甲基-d-吡喃甘露糖作为糖基供体被激活时，这种活性糖基物质 (35) 在低温 NMR 实验中是可观察到的。当脱水糖基化反应在三氟甲磺酸清除剂 2-氯吡啶存在下进行时，
• Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and ¹H, ¹³C, and ¹⁹F NMR Spectroscopic Investigation
  作者：David Crich、Sanxing Sun

  DOI：10.1021/ja971239r

  日期：1997.11.1

  The title question is addressed by low-temperature H-1, C-13, and F-19 NMR spectroscopies in CD2Cl2 as well as by the preparation of authentic samples from glycopyranosyl bromides and AgOTf. At -78 degrees C glycosyl triflates are cleanly generated with either nonparticipating or particpating protecting groups at O-2. The glycosyl triflates identified in this manner were allowed to react with methanol, resulting in the formation of methyl glycosides. Glycosyl triflates were generated at -78 degrees C in CD2Cl2 and allowed to warm gradually until decomposition was detected by H-1 and F-19 NMR spectroscopy. The decomposition temperature and products are functions of the protecting groups employed.